People seem to be inexhaustibly curious about what kind of pencil an artist does her drawing with, or which particular brand of pen† an author uses to write.

The digital tool kit is not so alluring or tactile, but I'm going to write up my process in a series of short posts, for my own future reference if nothing else.

It's interesting to note at this point that writing on the subject of writing has made the tone of this article somewhat pontificous thus far.

Shit. I'll try and snap out of it. (And 'pontificous' isn't even a real word anyway).

It's often said that good writers write like they talk — so the litmus test for me is always to read a draft out and see if it sounds natural.

Tools of the trade

After a brief fling with Google Docs—which is little use without an interenet connection and thus rejected—Textmate became my writing tool of choice, mostly because I'd already bought it for coding websites (and I liked its light-on-dark 'Blackboard' theme).

More recently I've switched again to Ulysses, a purpose-built writing app that has some nifty features like the ability to export straight to ebook/PDF format.

Here's a screenshot of how an article stub might look in Ulysses, with the ominously named 'Dark' theme activated:

There are a couple of neat Ulysses features to point out here: the @: prefix at the top of the document is used to edit the file name, and the selected line is showing hidden characters (spaces and paragraph breaks).

Why I format my writing with Markdown

You've probably noticed that the list in the screenshot uses asterisks instead of normal bullet points. This is because I'm using Markdown, a lightweight text formatting syntax which allows plain text to be converted into semantic HTML.

If that sounds complicated, it means you can do stuff like write #Catchy article headline and then rely on your software (in my case Squarespace) to convert it to <h1>Catchy article headline</h1> when you hit the publish button.

I first started using Markdown seriously—in conjunction with the Leanpub publishing platform—to write How to Reset Your Brain's Operating System at the end of last year, and quickly realised it would make sense to do all my writing with it.

The main selling point of Markdown for me is portability: it works with Squarespace out of the box, and with Wordpress via plugins like WP-Markdown, and hopefully one day with my mailing list software MailChimp too. If you've ever posted text from Microsoft Word into a CMS, you'll know what a headache formatting can be when switching platforms.

A quick note on Leanpub — although it's a brilliant tool for quickly iterating out a book (and even selling it before its finished), I'm now using Gumroad to sell my book, because it gives me access to the emails of my buyers. Leanpub acts more like Amazon, in that you aren't able to 'see' who your buyers are unless they expressly choose to share their email address. This was a deal breaker because growing my mailing list (over and above any social media platform) is a key objective for me.

Beginnings and endings

At this point in the writing process, I haven't thought about the headline of the essay, or much on what the conclusion will be either. Experience suggests that ending with something actionable for readers to ponder over can be helpful, and perhaps a prompting question if I'm soliciting comments. For the headline I'll often write ten or more possible options before settling on one.

Whilst this probably sounds quite straightforward, I should point out that often an article stub, or even a single sentence, will sit in my drafts folder for several weeks or months before I come back to it.

This particular article was written off the cuff this morning without any outlining, and given that it's an article about another article, now seems a good place to stop before things get too meta.


(To be continued... in Part 2 I'll start fleshing out the article in the screenshot, possibly with a video so you can see what happens)


† Did you know that Game of Thrones author George R.R. Martin writes on an ancient DOS-based computer? (But has another internet-connected machine for everything else other than writing). I think he could be onto something....


Posted to Writing in 2015.

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